Following Park (2017)’s seminal research on the types of the Google translator’s translation errors, this research aims at providing an in-depth analysis of the Google translator’s patterns in translating sentences with syntactic or semantic ambiguities. The specific goals of this study are three-fold. First, based upon the previous study of Park (2017), this study attempts to address, in details, how the presence of a negative adverb ahn affects the translation of DPs with conjuncted embedded CPs or vPs. Second, how the Google translator perceives how a DP + ka functions syntactically when the pair appears in sentences with embedded clauses or TPs will be investigated. Lastly, this study also attempts to investigate how the Google translator translates sentences involving an element that moves over multiple embedded CP layers. Data from various sources were used. The findings of the data analysis show that Korean negative marker ahn affects the Google’s perception and translation of sentences with embedded CPs or vPs and that a DP + ka which appears in sentences with an embedded CP or TP is perceived to be either the subject of a matrix verb or that of an embedded clause or an embedded TP.